p-Fluoronitrobenzene → HCID 561240, compound

HRID 1074200Notes

Reaction equation

HRID 1074200 reaction equation
C[O-].[Na+].[SH:4][C:5]1[N:6]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:7]=[CH:8][N:9]=1.F[C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1>C(O)C>[N+:24]([C:21]1[CH:22]=[CH:23][C:18]([S:4][C:5]2[N:6]([CH2:10][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:7]=[CH:8][N:9]=2)=[CH:19][CH:20]=1)([O-:26])=[O:25]

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 10942334Sodium Methoxide2×HCID 178527871HCID 178527871, compound

Product 1

HCID 561240HCID 561240, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 0.85 g (15.8 mmoles) of sodium methoxide and 15 ml of ethanol was refluxed for 5 minutes and then cooled to room temperature. To this solution was added 1.5 g (7.9 mmoles) of 2-mercapto-1-phenylmethylimidazole. After stirring for 10 minutes, 1.1 g (7.9 mmoles) of 1-fluoro-4-nitrobenzene was added and the mixture refluxed for 4 hours. An additional 0.85 g of sodium methoxide was added and the mixture refluxed for 9 hours. The mixture was filtered and the filtrate cooled and the resulting precipitate collected by filtration. The solid was recrystallized from dichloromethane/methanol to give the product as beige prisms, mp 122°-123° C.

Workup

  1. temperaturewas refluxed for 5 minutes
  2. temperaturethe mixture refluxed for 4 hours
  3. temperaturethe mixture refluxed for 9 hours
  4. filtrationThe mixture was filtered
  5. temperaturethe filtrate cooled
  6. filtrationthe resulting precipitate collected by filtration
  7. customThe solid was recrystallized from dichloromethane/methanol

Sources & evidence

ORD record
ord-a2732c3186ce479ba5d06e3629e92c89
Source dataset
uspto-grants-1990_11
Patent number
US04973599

Reaction notes

Loading…